


The Best Upper Sets Do It

by partypaprika



Category: Gossip Girl (TV 2007)
Genre: F/M, Treat
Language: English
Status: Completed
Published: 2020-02-14
Updated: 2020-02-14
Packaged: 2021-02-19 12:22:38
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,485
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22710763
Author URL: https://archiveofourown.org/users/partypaprika/pseuds/partypaprika
Summary: Blair had always been weird, but this wasweird, even for her.“I’m sorry, can you go through that again?” Dan asked. He couldn’t be hearing Blair right.“I need you to pretend to be my boyfriend for my work’s holiday party,” Blair said, her voice that special combination of slow and derisive that she used when she thought Dan was being especially dim.“That’s what I thought you said,” Dan said. “But I was convinced that it couldn’t be real since the last time turned out so poorly.”
Relationships: Dan Humphrey/Blair Waldorf
Comments: 14
Kudos: 138
Collections: Chocolate Box - Round 5





	The Best Upper Sets Do It

**Author's Note:**

  * For [shopfront](https://archiveofourown.org/users/shopfront/gifts).



> shopfront, I hope you enjoy!

Blair had always been weird, but this was _weird_ , even for her.

“I’m sorry, can you go through that again?” Dan asked. He couldn’t be hearing Blair right.

“I need you to pretend to be my boyfriend for my work’s holiday party,” Blair said, her voice that special combination of slow and derisive that she used when she thought Dan was being especially dim.

“That’s what I thought you said,” Dan said. “But I was convinced that it couldn’t be real since the last time turned out so poorly.”

Blair tilted her head, absorbing the hit, and then, like all things that Blair Waldorf did not particularly care to hear, dismissed it. “Irrelevant,” she said. “In fact, that just makes our dating now all the more believable. Old flames who reconnected.”

Dan had been half-in-love with Blair for almost ten years. He wasn’t concerned about believable. Dan took a deep breath and pushed those feelings down, deep down, until he could almost think critically about the situation. “Let’s rewind for a second, Iago, and put the scheming aside. Why do you need a boyfriend for your holiday party? Last time that I checked, we’re not living in the 1950s and no one is going to care if you don’t turn up with a trophy husband on your arm.”

“Trophy husband and you are not two things that are equal,” Blair said, stepping into the neat opening that Dan had given her. She might have said it cruelly once upon a time, but there was no mistaking the fondness in her voice now. It was probably why Dan gave her those openings again and again. Blair made him work hard for her smiles, but they were always worth it.

“For someone who’s trying to convince me that I should do you a favor, you’re not starting out with your best foot forward,” Dan said.

Blair huffed out a breath. “Up until a few months ago, Christoff Versteeg, the executive editor who essentially makes all hiring and promotional decisions, had barely known that I existed. I’d been trying for ages to try and build a relationship with him—I’d gotten nothing. And you know how good I can be at work relationships.” Dan shot her a look that Blair glared at. “What? They may not like me, but I know how to get people to work with me. Regardless, nothing. And then, out of nowhere, Christoff came to my office, asked me to go to lunch and then offered to set me up on a blind date a few months ago. Apparently, one of his nephews had read my work and wanted to go on a date with me.”

Dan raised his eyebrows at that.

“I can’t fault his taste, obviously,” Blair said. “But I know the way of blind dates and that way is disaster. I especially do not want to ruin any burgeoning relationship with Christoff through that. So, I told him that I was flattered but that I had a boyfriend.”

“Why can’t you have broken up with this boyfriend between then and now?” Dan asked. “And then you can just say that you’re too devastated to start dating again if anyone asks.”

“Because I floundered when he asked who I was dating,” Blair said and subtly looked down at the ground. Dan zeroed in on that. That was a sign of embarrassment and shame. A feeling of foreboding passed through Dan.

“How did you flounder?” Dan asked.

“I told him you were my boyfriend,” Blair said in one rush and then continued on, her words running together, “and it turns out that he loves your books and thinks you’re amazing.”

Dan stopped short, genuinely taken aback. “You deliberately, in a non-life-threatening situation, said that you were dating me?”

“I floundered,” Blair hissed. “And now we get coffee regularly but you’ve also never come to any events that I’ve attended for work and I think he’s starting to get suspicious. Are you going to help me or not?”

Dan took a minute, absorbed it all. He couldn’t deny that there was a little plume of satisfaction that Blair had said that they were dating. To someone else. As a counterweight, there was also the sinking lead feeling of reality that they were in fact doing no such thing and were unlikely to ever do that thing again.

“Dan,” Blair said, her voice soft. “Please.”

Dan’s heart clenched. For one minute, he envisioned himself saying no to yet another one of Blair’s schemes. One might have thought that she would have grown out of them. One would have been wrong. Finally, he sighed. It wasn’t like he was ever going to be able to say no in the first place. “Alright,” he said. “But you owe me. Big.”

“The biggest,” Blair agreed and she looked completely relieved. She took a deep breath. “Ok, let’s talk about outfits.”

Dan groaned.

The Conde Nast Publications holiday party was being held at the New York Public Library on a Saturday night. Blair had insisted that Dan meet at her place to get ready, so Dan showed up and the doorman, Stanley, waved Dan in after Dan asked about how his grandchildren were doing.

“Oh good, you’re here,” Blair said when she opened the door for Dan. She wore a green ombre dress with one strap over her left shoulder and her hair back in a French twist. The strap was dark green and it lightened all the way to the bottom, shimmering slightly as she moved. As always, she looked devastatingly gorgeous in it.

“This was the time that you told me to show up at, so you have no one but yourself to blame if you wanted me here earlier,” Dan said.

Blair made a face at that. “Why are you always so contrary?”

“I could ask you the same thing,” Dan said. “Show me to my dressing room.”

Blair directed Dan to her guest room where a Zegna tuxedo was laid out for Dan, complete with cufflinks, bowtie, socks and shirt. “I think that I got your measurements right,” she said. “But I have a few backups just in case.” Blair, always prepared.

“You missed your calling as a boy scout,” Dan said and began shrugging out of his shirt. When he’d gotten it off, he saw Blair still standing there, her eyes trained on him, and felt himself go hot. Blair abruptly looked away, her cheeks spotted with red, and Dan cleared his throat.

“Right, I’ll just be outside,” Blair said. “Just, uh, let me know if anything doesn’t fit.”

Blair hadn’t been wrong—the clothing fit him like a glove—and when he emerged from the guest bedroom, Blair stopped gratifyingly short, her cheeks going even redder as she looked Dan over.

“Yes, that’s uh—” Blair grasped for words and Dan forced himself to keep in the smile that was brimming on his lips. Exceedingly gratifying. “Good. That’s good,” Blair finally got out.

“All the credit goes to you,” Dan said magnanimously.

They arrived at the New York Public Library just as a host of other cars arrived, spitting out their passengers. Someone else called for Blair as they got out. Dan expected Blair to go over and say hi, leaving him behind to make his way over. But Blair waited for Dan to get out of the car and reached for his hand instead, twining their fingers together. She gently pulled Dan over to the group, three women and two men. She seemed to know everyone in the group, smiles, hugs and kisses all around, introducing Dan as her boyfriend, but never letting go of Dan’s hand.

Dan couldn’t help but focus on Blair's hand in his, all of the names that Blair said going completely unlearned. It was a warm brand in his hand, his pulse beating so loudly, he was surprised that Blair didn’t comment on it. Eventually the group turned to go into the library—although Dan had been to the library more times than he could count, he’d never been here at night and as they stepped through the entrance, it felt like a world transformed.

“A magazine publisher doing their party at a library,” Dan said to Blair. “I like it.”

Blair preened, as if she’d been the one to pick out the location—and maybe, knowing Blair, she had had something to do with it. “It is beautiful,” she agreed. “And thank you for coming with me tonight.” She squeezed his hand once and for a moment, Dan let himself look at Blair, his heart beating fast.

“Of course,” Dan said eventually.

Someone jostled Blair and she shook her head, as if clearing out the cobwebs. “Come on, Humphrey, we’ve got places to go and people to see.”

First up, of course, was the famed Christoff who Blair contrived to run into near one of the open bars.

“Oh, Christoff!” Blair said with both surprise and delight in her face. Dan did his best to keep from rolling his eyes. “Happy holidays. Have I ever introduced you to my boyfriend? This is Dan Humphrey.”

Christoff was a man of medium height, who looked like he’d once been in fighting shape but middle age had started to creep its way and softened his edges.

“Dan Humphrey,” Christoff said, his voice verging on gleeful. “I love your books. A friend gave me _The Winter Finch_ and I have been obsessed since.”

“Thank you,” Dan said, genuinely meaning it. He did alright as an author, enough to support himself most of the time through his writing, but it was rare that someone was moved about his works enough to say something to him. At least rare for people that didn’t want something from him.

They chatted with Christoff for a while, standing near the bar and getting refills of champagne. Surprisingly, Blair made their excuses, saying that they needed to grab some food, after a little more than twenty minutes. Dan raised his eyebrows as soon as they were out of earshot.

“I would have thought that you wanted all the facetime that you could get with Christoff,” Dan said.

“Are you saying that you don’t want to eat?” Blair asked.

“I’m not saying that,” Dan said. “I would have been fine if you wanted to continue to talk to Christoff. He wasn’t so bad.”

“You’re just saying that because he likes your writing and marks mine up with red,” Blair said.

“Well, when you put it like that…” Dan said and Blair laughed.

“Do you want me to show you where the food is or not?” Blair said, trying to make her expression stern.

“Lay on, Macduff,” Dan said theatrically, laying his hand across Blair’s, making Blair smile all over again.

After helping themselves to one of the food stations (sushi), they found a few open seats at a table at sat down. “What do you think of it so far?” Blair asked.

It was a lot more fun than Dan had expected, but he wasn’t going to say that to Blair, at least not yet. If he gave in too easily, she’d take it as ammunition the next time.

“It’s not bad,” Dan said. “Who’s our next target?”

“We’ll just mingle around the room,” Blair said. Dan squinted at Blair. No agenda?

“No on in particular?” Dan asked, trying to keep the suspicion out of his voice.

“I’d love for you to meet my direct boss, Jen. Oh, did you see the s’mores station?” Blair asked.

Dan whipped his head around. “No! There’s a s’mores station and we didn’t start there?”

Blair laughed at that. “Come on, I spotted it near the back.”

They spent the rest of the evening mingling some, but also trying the wide variety of custom cocktails, desserts and treats at different stations around the room. “This is a good party,” Dan said, on the verge of tipsy, several drinks later.

“Yeah, it is a good party,” Blair agreed. “Thank you for coming with me.”

“Thank you for inviting me,” Dan said automatically and then his thoughts caught up with him. “Wait, Blair, we have done surprisingly little mingling and you could have gotten some serious time in with Christoff.”

Blair froze and that confirmed it for Dan. Dan tried to think it out logically, but he kept getting back an answer that made his heart jump around in his chest as if it were auditioning for tachycardia. “If I’m getting this completely wrong, I apologize in advance,” he said slowly, “but did you invite me here to be your actual date?”

Blair looked guilty as hell. “Why didn’t you just ask me to be your date?” Dan said.

Blair sighed. “Dan, we have so much history. And I was the one who messed things up last time. I don’t know, I thought that maybe I could show you that we could be good again. That we would be good again. That I knew how lucky I would be to date you. Anyone would—but I wanted it to be me.”

“I think that there were a lot of reasons why our last attempt turned out so disastrously,” Dan said. “Although I’m happy to give you as much blame as you would like. But you don’t have to let me do a trial run of dating you. As embarrassing as it is, if you say you’re in, I’m in too.”

Blair looked up at Dan, her eyes focused on Dan, and Dan wanted to drink it all in, have Blair look at him forever. She carefully placed her hands on Dan’s shoulders, sliding them up his neck and gripping the back of Dan’s head, bringing the two of them close. Dan tried not to shiver at how good that felt and did not succeed.

“So, this is a date,” Blair said.

“Yes,” Dan agreed.

“And people kiss on dates,” Blair said.

“They do,” Dan said.

And Blair blessedly closed the distance between the two of them, kissing Dan, opening her mouth and slotting the two of them together as if they needed to make up for lost time right then and there.

On the cab ride home, Blair half-asleep against Dan’s shoulder and her right hand enclosed in Dan’s as he marked circles on her skin, Blair asked, “Good first date?”

“Depends on where the next one is,” Dan said. “You’ve set some high expectations. Are you planning on taking me to the Eiffel Tower next?”

“I was thinking of pushing you off Niagara Falls,” Blair said.

“But now I have proof that you don’t mean it,” Dan said. “You’ve asked me out on a date and introduced me as your boyfriend in public.”

“I’ve made a grave mistake,” Blair said, but she lifted her head off of Dan’s shoulder to kiss him gently again and Dan thought his heart might burst with happiness.


End file.
